Cbz-Pentafluoro-L-Phenylalanine is a Cbz-protected, L-phenylalanine-derived amino acid derivative bearing a pentafluorinated phenyl side chain, classifying it as an unnatural, structurally modified aromatic amino acid. The molecule contains a free carboxyl group and an amino group masked as a benzyloxycarbonyl (Cbz) carbamate, while the pentafluorophenyl substituent provides strong electron-withdrawing character and altered hydrophobic/aromatic interaction properties relative to unmodified phenylalanine. In peptide synthesis workflows, the Cbz protection pattern supports chemoselective handling of the amino functionality and the fluorinated aromatic side chain provides a handle for structure-property studies, analytical method development, and incorporation into synthetic peptide analogues for chemical biology investigations.
CAT No: CP16208
Cbz-Pentafluoro-L-Phenylalanine is an N-Cbz protected L-phenylalanine derivative in which the phenyl ring is fully fluorinated to a pentafluorophenyl group, yielding a chiral amino acid framework with a stereodefined α-carbon. The molecule contains a benzyloxycarbonyl (Cbz) carbamate on the amino functionality and a free carboxylic acid, providing orthogonal handles for peptide coupling and subsequent deprotection. The pentafluorophenyl side chain introduces strong electron-withdrawing character and distinctive aromatic reactivity, which can influence coupling conditions, amide formation outcomes, and downstream derivatization. The combination of protected amine, carboxylic acid, and a fluorinated aromatic motif makes the compound a practical chiral intermediate for peptide building block preparation and for constructing fluorinated analogs used in synthetic and analytical workflows.
1. Peptide Synthesis
Cbz-Pentafluoro-L-Phenylalanine is applied in peptide synthesis workflows where N-protection and a stereodefined amino acid backbone are required for controlled amide bond formation. The Cbz carbamate protects the α-amino group during coupling, while the free carboxylic acid participates as the acyl partner to generate peptide bonds under standard peptide coupling chemistries. The pentafluorophenyl side chain can be incorporated as a fluorinated residue to tune aromatic electronics and to support later functionalization or spectroscopic tracking. The resulting fluorinated peptide fragments and full-length sequences can serve as research-grade peptide building blocks for structure-activity relationship studies and for producing fluorinated analog libraries.
2. Amino Acid Derivatization
Cbz-Pentafluoro-L-Phenylalanine supports amino acid derivatization strategies that exploit the protected amine and the electron-poor pentafluorophenyl aromatic ring. The Cbz group enables selective deprotection to reveal the free amine for further transformations such as additional protection, conjugation handles, or orthogonal functionalization. The pentafluorophenyl moiety can undergo nucleophilic aromatic substitution or related aromatic substitution chemistry, enabling side-chain installation of linkers, tags, or reactive substituents while retaining the α-amino acid stereocenter. Downstream derivatives generated from this platform can function as intermediates for fluorinated small molecules, peptide analogs, and chemical biology probes requiring defined stereochemistry and a chemically addressable aromatic scaffold.
3. Chemical Biology Probes
Cbz-Pentafluoro-L-Phenylalanine is suitable for chemical biology research that relies on fluorinated amino acid incorporation to create traceable or electronically tuned biomolecular analogs. The molecule's protected amino acid structure allows incorporation into peptides or peptide-like constructs through peptide coupling, while the pentafluorophenyl aromatic ring can act as a chemically reactive motif for subsequent conjugation to nucleophiles or affinity tags. The Cbz-protected nitrogen permits staged synthetic assembly, including deprotection at a chosen step to enable controlled attachment of labels or capture reagents. Fluorinated peptide conjugates prepared from this intermediate can be used to generate molecular probes for studying binding interactions, substrate recognition, or biomolecular assembly in biochemical research settings.
4. SAR Studies
Cbz-Pentafluoro-L-Phenylalanine is used in structure-activity relationship studies where fluorinated aromatic residues help probe electronic and steric contributions to molecular recognition. The stereodefined L-configuration and the presence of a free carboxylic acid enable consistent incorporation into peptide scaffolds, allowing systematic substitution of the pentafluorophenyl side chain at defined positions. The electron-withdrawing pentafluorophenyl group can modulate hydrogen bonding patterns, aromatic interactions, and local conformational preferences in peptide analogs. Fluorinated analog series derived from this amino acid intermediate can feed SAR workflows by enabling comparative analysis of structure-dependent behavior across related peptide and peptidomimetic structures.
5. Pharmaceutical Manufacturing Intermediates
Cbz-Pentafluoro-L-Phenylalanine is relevant to pharmaceutical manufacturing and fine chemical synthesis as a chiral, protected amino acid intermediate for producing fluorinated peptide intermediates and process-ready building blocks. The Cbz protection strategy supports controlled handling during synthetic steps, while the free carboxylic acid enables conversion into activated derivatives or direct coupling partners in manufacturing-scale peptide assembly. The pentafluorophenyl side chain can be maintained through protected synthesis sequences and later used for downstream derivatization steps that require the aromatic fluorinated motif to remain intact. Industrially, this compound can serve as a defined stereochemical input for producing fluorinated drug-like intermediates, analytical standards, or process intermediates used in the manufacture of peptide-based or peptide-adjacent chemical entities.
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